Would there be any reason that I can’t use the Taxonomies option for a sidebar to have it show on certain pages that I assign a specific category too (using the plugin Post Tags and Categories for Pages to enable this)? It works if I assign the sidebar specifically to the page but not if I use the category taxonomy that I assigned to the same page.
The sidebar will be enabled in the archive page only and not the taxonomy’s single posts. For that, you need to enable it individually in Pages and Posts.